Chief of Staff

Chief of Staff

Philadelphia, PA

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About the Client

The company builds Virtual Bid Assistants for commercial glazing and architectural metals contractors. Their software plus services pulls scope out of RFPs, manages RFIs, and generates proposals so estimators stop missing deadlines and start winning the work they actually want.

The business is currently at roughly $2M ARR, targeting $5M by the end of 2026 and $30M by the end of 2027. Backed by leading early-stage investors and headquartered in Philadelphia.

About the Role

The company is on the path from ~$2M to $30M ARR over the next twenty-four months. That kind of growth requires a real operating system underneath it.

The Chief of Staff will serve as the CEO's partner in building and running that system: the cadence, the back-office, the recruiting pipeline, the investor reporting, and the connective tissue across engineering, sales, and customer success.

This is the operator who turns founder velocity into company velocity.

Responsibilities

• Run the operating cadence. Weekly staff meetings, agendas, action tracking, dashboards, and OKRs
• Own the finance and compliance stack. QuickBooks cleanup, payroll, state filings, and coordination with state agencies to ensure proper filings and compliance
• Build SOPs that allow future hires to operate systems independently
• Hire and manage an Executive Assistant and additional administrative support as the company scales
• Design and document the operating system that takes the company from startup stage to a scalable organization
• Codify successful workflows into repeatable processes across the business
• Partner with the CEO on fundraising preparation, including investor updates, KPI tracking, data room management, and Series A narrative development
• Quarterback hiring efforts across the company in partnership with external recruiting firms
• Coordinate candidate screening, scheduling, interview prep, and debrief processes
• Stand up internal tooling, including AI-native operations tooling, dashboards, and internal systems hygiene
• Serve as the connective tissue between engineering, sales, customer success, and the executive team

First 90 Days

Success in the first 90 days will be measured against three core deliverables:

• Payroll and compliance SOP built and operational
• Executive Assistant hired and onboarded
• Company knowledge base built and organized to support rapid onboarding and scaling

Requirements

Must-Haves

• 4 to 8 years of experience with a strong track record of execution
• Backgrounds may include top-tier management consulting, private equity portfolio operations, prior Chief of Staff experience at a high-growth company, Capitol Hill staffing experience with a follow-on MBA, or junior military officer experience followed by an operating role
• Exceptional organizational skills with the ability to manage multiple priorities simultaneously
• Builder mentality — focused on creating systems and executing, not over-planning
• Comfortable owning broad operational scope end-to-end in a highly hands-on environment
• Strong written and verbal communication skills with the ability to represent the CEO and company externally
• Fluency with modern AI tooling including Claude, Claude Code, agents, and AI-native workflows

Nice-to-Haves

• Veteran or prior service background
• Operating experience at an early-stage startup, especially in vertical SaaS or AEC-tech
• MBA from a top-tier program such as Wharton, HBS, or similar institutions

Compensation & Benefits

• Base Salary: $150K–$200K
• Equity: early-employee equity grant with significant upside tied to company growth trajectory

Philadelphia preferred, with an in-person presence expected the majority of the week.

Open to NYC-based candidates who can travel to Philadelphia two days per week.

Remote-only candidates are not a fit for this role.